WO2004087811A1 - Compositions de resine epoxyde ignifuges, preimpregnes et stratifies metallises - Google Patents

Compositions de resine epoxyde ignifuges, preimpregnes et stratifies metallises Download PDF

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Publication number
WO2004087811A1
WO2004087811A1 PCT/JP2003/003811 JP0303811W WO2004087811A1 WO 2004087811 A1 WO2004087811 A1 WO 2004087811A1 JP 0303811 W JP0303811 W JP 0303811W WO 2004087811 A1 WO2004087811 A1 WO 2004087811A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy resin
retardant
flame
halogen
metal
Prior art date
Application number
PCT/JP2003/003811
Other languages
English (en)
Japanese (ja)
Inventor
Takeshi Koizumi
Kenji Ogasawara
Keiko Kashihara
Mao Yamaguchi
Original Assignee
Matsushita Electric Works, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Matsushita Electric Works, Ltd. filed Critical Matsushita Electric Works, Ltd.
Priority to PCT/JP2003/003811 priority Critical patent/WO2004087811A1/fr
Priority to AU2003227256A priority patent/AU2003227256A1/en
Publication of WO2004087811A1 publication Critical patent/WO2004087811A1/fr

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Classifications

    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/01—Dielectrics
    • H05K2201/0104—Properties and characteristics in general
    • H05K2201/012—Flame-retardant; Preventing of inflammation
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203—Fillers and particles
    • H05K2201/0206—Materials
    • H05K2201/0209—Inorganic, non-metallic particles
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
    • H05K2203/12—Using specific substances
    • H05K2203/122—Organic non-polymeric compounds, e.g. oil, wax, thiol

Definitions

  • the present invention relates to a flame-retardant epoxy resin composition, a pre-preda and a metal-clad laminate, and more particularly, to an epoxy resin composition and a pre-prepa, each of which does not contain a halogen element and has excellent flame retardancy. And metal-clad laminates. Further, the present invention relates to a printed wiring board and a multilayer printed wiring board using a metal-clad laminate.
  • Thermosetting resins such as epoxy resins
  • epoxy resins are widely used as printed wiring board materials and semiconductor encapsulating materials because of their excellent adhesive properties, electrical insulation properties, and chemical resistance.
  • compounds containing a halogen element such as bromine are generally compounded in order to impart flame retardancy to fire.If halogens such as bromine are introduced in this way, excellent flame retardancy is achieved. It is widely known that the cured product shown can be obtained.
  • the cured product of the thermosetting resin composition containing such an orogen-containing flame retardant may generate harmful substances such as hydrogen halide when burned, and may be used in humans, organisms, and the natural environment.
  • has the disadvantage of adversely affecting epoxy resins and epoxy resin compositions that do not contain halogen elements and exhibit excellent flame retardancy have been widely developed.
  • the halogen-free flame retardant include phosphorus compounds and metal hydroxides.
  • the performance of electronic devices has been remarkably improved, and the characteristics of printed wiring board materials, particularly the dielectric constant and dielectric loss tangent, are increasingly affecting the design and operation of devices.
  • the dielectric constant of the printed wiring board is increased, the electric signal flowing through the circuit is slowed down, which may cause a malfunction of the circuit or a failure of the circuit.
  • the dielectric loss tangent increases, the amplitude of the electric signal deteriorates, which also causes a malfunction of the circuit.
  • Laminated board for high performance circuit and accurate operation Materials are generally required to have a low dielectric constant and a small dielectric tangent.
  • the dielectric constant of general glass epoxy laminates currently on the market is approximately 4.5 to 5.0, and the dielectric constant of the laminate material is desirably 5.0 or less.
  • Aluminum hydroxide which is a widely used metal hydroxide flame retardant, has a dielectric constant of about 8.7, which is higher than that of general glass epoxy laminates. Therefore, by adding to the epoxy resin composition as a raw material, the dielectric constant of the laminate material is increased.
  • phosphorus-modified epoxy resins have higher dielectric constants than conventional epoxy resins, and the dielectric constants of pre-predaders, resin-coated copper foils and laminates using these as main components are also high.
  • the dielectric constant is higher than that of the conventional one.
  • phosphaphenanthrene compounds are more expensive than general brominated flame retardants and brominated epoxy resins.
  • Non-halogen flame-retardant printed wiring board materials containing a large amount of such components have higher dielectric constants than conventional halogen-based flame-retardant printed wiring board materials, causing electrical signal delays. If the circuit configuration is the same as that of the product, the electronic device may not be driven or malfunction, and may not be put to practical use. Disclosure of the invention
  • An object of the present invention is to provide a non-housing material having excellent flame retardancy, which has a dielectric constant equivalent to that of a conventional halogen-based flame-retardant printed wiring board material, has a small dielectric loss tangent, can be manufactured industrially at low cost.
  • An object of the present invention is to provide a gen-based flame-retardant printed wiring board material.
  • the present invention provides:
  • ⁇ is the same or different and is an alkyl group having 1 to 3 carbon atoms.
  • Non-halogen flame-retardant epoxy resin composition containing
  • a non-halogenated flame-retardant pre-predder obtained by impregnating a substrate with a non-halogenated flame-retardant epoxy resin composition according to the present invention and semi-cured,
  • a non-halogen-based flame-retardant metal-clad laminate comprising at least one of the above-mentioned non-halogen-based flame-retardant pre-preda and a metal foil laminated on at least one surface of the flame-retardant pre-prepader,
  • Non-halogen flame retardant formed by forming a circuit on at least one surface of the metal-clad laminate Printed wiring board, and
  • non-halogen flame-retardant multilayer printed wiring board formed by combining the above printed wiring board, the above-mentioned non-halogen flame retardant pre-preda and a metal foil, and heating and pressing.
  • the (a) aromatic condensed phosphate ester flame retardant used in the present invention has the formula:
  • ⁇ is the same or different and is an alkyl group having 1 to 3 carbon atoms.
  • PX-200 manufactured by Daihachi Chemical Co., Ltd.
  • PX-200 is an example of the condensed aromatic phosphate having such a structure.
  • the addition amount of the aromatic condensed phosphate ester flame retardant is preferably 10 to 40 parts by weight, more preferably 20 to 30 parts by weight, based on 100 parts by weight of the total amount of the epoxy resin and the lubricating agent. Parts by weight. If the added amount is less than 10 parts by weight, a sufficient flame retardant effect cannot be obtained, and if it exceeds 40 parts by weight, the heat resistance and moisture resistance of the resin-hardened material are reduced and cannot be put to practical use.
  • the epoxy resin has at least two epoxy groups in the molecule, and may be any resin as long as it does not contain a halogen element.
  • epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, and polyvalent phenol.
  • a combination of a bisphenol A type epoxy resin and a nopolak type epoxy resin is preferable as the epoxy resin. Further, from the viewpoint of adjusting the dielectric constant, which is the object of the present invention, a cresol novolak epoxy resin having a low dielectric constant among novolak epoxy resins is more preferable.
  • the type of the metal hydroxide (d) used in the present invention is not particularly limited as long as it can impart flame retardancy to the resin composition, but aluminum hydroxide, magnesium hydroxide and the like are preferable. These include those that have been surface-treated with a silane coupling agent, for example, a silane coupling agent such as epoxy silane, amino silane, vinyl silane, mercapto silane, or those in which a metal such as nickel is dissolved. included.
  • Aluminum hydroxide is preferable as the metal hydroxide because of its high flame retardancy. However, since aluminum hydroxide has a high dielectric constant, the addition of a large amount thereof increases the dielectric constant of the resin composition.
  • magnesium hydroxide cannot provide sufficient flame retardancy by itself because it is inferior to aluminum hydroxide in flame retardant effect, but its dielectric constant is lower than that of aluminum hydroxide. Therefore, by using both in combination, flame retardancy can be imparted without increasing the dielectric constant.
  • the addition amount of the metal hydroxide (d) is preferably 20 to 100 parts by weight, more preferably 30 to 8 parts by weight, based on 100 parts by weight of the total amount of the (b) epoxy resin and (c) the resin curing agent. 0 parts by weight. If the amount of the metal hydroxide is less than 20 parts by weight, a sufficient flame-retardant effect cannot be obtained. If the amount is more than 100 parts by weight, the adhesive strength of the resin-hardened resin is reduced, and it cannot be put to practical use.
  • Examples of the resin curing agent (c) used in the present invention include dicyandiamide, phenol-type nopolak resin, cresol-type nopolak resin, bisphenol A-type nopolak, and a triazine ring-containing novolak resin. These may be used alone or in combination. Although not particularly limited, when burning A triazine ring-containing novolak resin that generates nitrogen gas is preferable from the viewpoint of flame retardancy. From the viewpoint of the dielectric constant, among the triazine ring-containing novolak resins, a triazine ring-containing cresol novolak resin is more preferable.
  • the amount of the resin curing agent to be combined is not particularly limited, but it is desirable to mix the epoxy resin equivalent to 0.3 to 1.5 with respect to the hydroxyl equivalent of the resin curing agent. Outside this range, the resin hardener and the epoxy resin do not react sufficiently, resulting in reduced heat resistance and moisture resistance, and are not practical.
  • the hardener alone can be sufficiently hardened by heat and pressure molding, so a hardening accelerator is not necessarily required.
  • a hardening accelerator is not necessarily required.
  • a phenol-type novolak resin containing triazine ring is used as a curing agent, it can be sufficiently cured by heat and pressure molding under general conditions due to its reactivity.
  • a curing accelerator usually used for accelerating the curing of the epoxy resin is used.
  • the curing accelerator include imidazole compounds such as 2-ethyl-4-methylimidazole. These curing accelerators can be used alone or in combination of two or more.
  • the curing accelerator may be used in an amount sufficient to promote the curing of the resin composition, and those skilled in the art can appropriately select the amount.
  • the flame-retardant epoxy resin composition of the present invention can be produced from the above components by the same method as the conventional method for producing an epoxy resin composition.
  • the flame-retardant pre-preda of the present invention is produced by impregnating a substrate with an epoxy resin varnish comprising the flame-retardant epoxy resin composition of the present invention and drying the resin composition to obtain a semi-cured resin composition. .
  • the epoxy resin varnish means a liquid obtained by dissolving or dispersing the above epoxy resin composition in an appropriate solvent.
  • the solvent include ketone solvents such as methylethyl ketone, alcohol solvents such as methoxypropanol, and amide solvents such as dimethylformamide.These solvents are used alone or as a mixture of a plurality of solvents. be able to.
  • the semi-cured product refers to a product in which a curing reaction of the resin composition is partially advanced by a heat treatment by drying and B-staged.
  • a woven or nonwoven fabric of glass fiber or organic fiber can be used as the base material.
  • the impregnation amount of the epoxy resin composition is 30 to 65% by weight, preferably 40 to 55% by weight, based on the weight of the prepredder.
  • the impregnation can be performed by immersing the base material in the epoxy resin composition.
  • the epoxy resin composition may be applied to a substrate.
  • the flame-retardant metal-clad laminate of the present invention is obtained by laminating at least one, usually 1 to 9, and preferably 1 to 4 of the pre-preda of the present invention, and a metal foil (for example, Copper, silver, aluminum, stainless steel, and other metal foils) are laminated.
  • the thickness of the metal foil is usually 3 to 105 ⁇ .
  • the lamination of the metal foil can be performed in the same manner as in the case of laminating the metal foil on a pre-preda using an epoxy resin composition.
  • a metal foil is overlaid on a pre-preda and heated and pressed.
  • the flame-retardant printed wiring board of the present invention can be manufactured by forming a circuit on at least one surface of the metal-clad laminate of the present invention.
  • the flame-retardant multilayer printed wiring board of the present invention can be manufactured by combining the printed wiring board of the present invention, the pre-predator of the present invention, and, if desired, a metal foil (for example, a copper foil), followed by heating and press molding. it can.
  • a metal foil for example, a copper foil
  • Heating and pressurizing conditions may be appropriately selected in accordance with the conventional manufacturing method.
  • a printed wiring board, a pre-preda and a desired metal foil are arranged at predetermined positions, and a temperature of 170 ° C. and a temperature of 2 kgf are applied.
  • a pressure of / cm 2 heating and pressurizing may be performed for 90 minutes, but the conditions are not limited to these.
  • Example 1 As epoxy resin component (b), 51 parts by weight of bisphenol A type epoxy resin (epoxy equivalent: 480), 28 parts by weight of cresol nopolak resin (epoxy equivalent: 220), and 21 parts by weight of resin curing agent (c) Triazine ring-containing phenol novolak resin (hydroxyl equivalent 120), aromatic condensed phosphate ester flame retardant (a) 30 parts by weight of phosphate ester flame retardant (trade name PX-200, manufactured by Daihachi Chemical Co., Ltd.), metal hydroxide The product (d) was mixed with 50 parts by weight of aluminum hydroxide (trade name CL-303, manufactured by Sumitomo Chemical Co., Ltd.), and methyl ethyl ketone was added to the mixture so that the solid content became 65%. A resin varnish was prepared.
  • the varnish was applied to a glass woven fabric, impregnated, and dried at 160 ° C. for 5 minutes to produce a prepreg.
  • the varnish impregnation amount was 48% based on the weight of the pre-preda.
  • Eight pieces of the prepared pre-preda were superimposed, and copper foil with a thickness of 18 ⁇ m was arranged on both surfaces thereof, and was heated and pressed to obtain a 1.6-thick double-sided laminated board.
  • a copper-clad laminate was obtained in the same manner as in Example 1, except that 79 parts by weight of cresol novolak (epoxy equivalent: 220) was used as an epoxy resin component.
  • a copper-clad laminate was obtained in the same manner as in Example 1, except that 21 parts by weight of a triazine ring-containing cresol novolak resin (hydroxyl equivalent: 120) was used as a resin curing agent. Comparative Example 1
  • a copper-clad laminate was obtained in the same manner as in Example 1 except that 30 parts by weight of phosphaphenanthrene (trade name: HCA, manufactured by Sanko Co.) was used instead of the aromatic condensed phosphate ester flame retardant.
  • phosphaphenanthrene trade name: HCA, manufactured by Sanko Co.
  • a copper-clad laminate was obtained in the same manner as in Example 1, except that the addition amount of the phosphate ester flame retardant PX-200 was changed to 5 parts by weight. Comparative Example 3
  • a laminated laminate was obtained in the same manner as in Example 1, except that the addition amount of the phosphate ester flame retardant PX-200 was changed to 50 parts by weight.
  • a copper-clad laminate was obtained in the same manner as in Example 1, except that the amount of the metal hydroxide CL-303 was changed to 5 parts by weight.
  • a laminated laminate was obtained in the same manner as in Example 1 except that the addition amount of the metal hydroxide CL-303 was changed to 150 parts by weight.
  • the multilayer board was entirely etched and the flame retardancy of the multilayer board was evaluated according to the UL94-1 993 20 mm vertical test method.
  • the peel strength between the outermost copper foil and the insulating layer of the multilayer board was measured in accordance with JIS 6481 No5.7.
  • the adhesive strength between the glass cloths in the multilayer board was measured in accordance with JIS-6481N05.7.
  • the glass transition temperature (Tg) of the inner layer material was measured in accordance with JIS-6481 No 5.17.5.
  • Phosphate ester flame retardant 30 30 30 5 50 30 30 30 Aluminum hydroxide 50 25 50 50 50 50 5 150 150 Hydroxide 7 generator 25
  • the laminate obtained in the examples according to the present invention is a non-halogen flame-retardant copper-clad laminate, the combustion time in flame retardancy is short, and it is equivalent to V-0. is there.
  • hydroxide aluminum which has a relatively high dielectric constant, it achieves the same dielectric constant as conventional products.
  • the comparative example using the phosphorus compound flame retardant not included in the scope of the present invention has a higher dielectric constant than the conventional laminate material.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Un produit ignifuge de phosphate fondu aromatique représenté par la formule générale (a), dans laquelle, R1 à R8 sont identiques ou différents et représentent chacun alkyle C1-3 ; (b) une résine époxyde sans halogène possédant au moins deux groupes époxy par molécule; (c) un durcisseur de résine sans halogène, et (d) une composition de résine époxyde ignifuge non halogène contenant un hydroxyde de métal. Cette composition de résine époxyde possède une constante diélectrique comparable à celle de matériaux conventionnels de cartes imprimées ignifuges halogène, et possède cependant une excellente propriété ignifuge.
PCT/JP2003/003811 2003-03-27 2003-03-27 Compositions de resine epoxyde ignifuges, preimpregnes et stratifies metallises WO2004087811A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/JP2003/003811 WO2004087811A1 (fr) 2003-03-27 2003-03-27 Compositions de resine epoxyde ignifuges, preimpregnes et stratifies metallises
AU2003227256A AU2003227256A1 (en) 2003-03-27 2003-03-27 Flame retardant epoxy resin compositions, prepregs and metal-clad laminates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2003/003811 WO2004087811A1 (fr) 2003-03-27 2003-03-27 Compositions de resine epoxyde ignifuges, preimpregnes et stratifies metallises

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WO2004087811A1 true WO2004087811A1 (fr) 2004-10-14

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102582183A (zh) * 2011-12-29 2012-07-18 铜陵浩荣电子科技有限公司 一种无卤阻燃纸基覆铜板的制作方法
CN102732096A (zh) * 2012-07-10 2012-10-17 依利安达电子（昆山）有限公司 无卤阻燃无溶剂双固化油墨组合物及其制备方法
CN103525086A (zh) * 2012-07-04 2014-01-22 合正科技股份有限公司 高耐热、低刚性、难燃性树脂及其组合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0947547A1 (fr) * 1998-04-01 1999-10-06 Daihachi Chemical Industry Co., Ltd. Composition de résine retardatrice aux flammes
JP2002179887A (ja) * 2000-12-19 2002-06-26 Toshiba Chem Corp ハロゲンフリーの難燃性エポキシ樹脂組成物、並びにそれを含有するプリプレグ、積層板、銅張積層板およびプリント配線板
JP2003049051A (ja) * 2001-08-02 2003-02-21 Hitachi Chem Co Ltd 難燃性樹脂組成物及びその用途

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0947547A1 (fr) * 1998-04-01 1999-10-06 Daihachi Chemical Industry Co., Ltd. Composition de résine retardatrice aux flammes
JP2002179887A (ja) * 2000-12-19 2002-06-26 Toshiba Chem Corp ハロゲンフリーの難燃性エポキシ樹脂組成物、並びにそれを含有するプリプレグ、積層板、銅張積層板およびプリント配線板
JP2003049051A (ja) * 2001-08-02 2003-02-21 Hitachi Chem Co Ltd 難燃性樹脂組成物及びその用途

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102582183A (zh) * 2011-12-29 2012-07-18 铜陵浩荣电子科技有限公司 一种无卤阻燃纸基覆铜板的制作方法
CN103525086A (zh) * 2012-07-04 2014-01-22 合正科技股份有限公司 高耐热、低刚性、难燃性树脂及其组合物
CN102732096A (zh) * 2012-07-10 2012-10-17 依利安达电子（昆山）有限公司 无卤阻燃无溶剂双固化油墨组合物及其制备方法

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